
Family-friendly holiday rentals in Orillia
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Orillia
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

RELAX @ our HOT TUB and SAUNA in the woods
PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

Four season glamping dome under the stars
Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Charming Main Floor w Hot Tub
Welcome to our charming main floor apartment in the beautiful city of Orillia! This space is is suitable for families or small groups looking for a comfortable stay in a convenient location. This is a fully furnished home that features three bedrooms, one bathroom, a fully equipped kitchen with all the essentials needed to prepare your own meals. The living room is bright and cozy with a 43" Samsung Smart TV including Netflix, unlimited high speed internet and a spacious 6 seater dining table.

Hillside Haven: Serene Studio Retreat for 4
Escape to the serene Carriage Club Resort Studio! Dive into our inviting swimming pool, gather 'round the firepit, or challenge friends to volleyball. Stay active in our modern gym, then explore nearby skiing and golf. Pamper yourself at Vetta SPA or hit mountain biking and hiking trails. Your cozy studio, with a king-size bed and pull-out sofa, sleeps 4 comfortably. Nestled in rolling hills, just a 15-minute drive from Bass Lake's sandy shores. Discover tranquility with a touch of adventure!

Orillia TwnHse Oasis w King Bed
Have fun with the whole family at this stylish townhouse oasis. The townhouse features 3 bedrooms, 2.5 bathrooms and 4 beds. The principle bedroom has a king bed, the 2nd bedroom has a queen bed, and the third bedroom has a queen bunk bed (qn bttm, qn top). The house features a large deck with a gas bbq, outdoor dining, and lots of lounging space. Right behind the townhouse is a beautiful nature ravine with lots of trails. Come, enjoy and relax. The property offers super high speed internet.

Cozy Deluxe Studio at Horseshoe Valley
Welcome to Horseshoe Valley, just 1.5 hrs north of Greater Toronto Area. It's a four-season wonder of nature with limitless access to lakes, rivers, trails, and rolling hills. Whether you aim to ski in snow-laden forests of pine, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

Bright basement apt with private entrance, Barrie
Welcome to Your Bright Basement Retreat in Barrie! Our cozy and modern 2-bedroom basement apartment offers the perfect balance of comfort and privacy. Located in a quiet residential neighborhood, it’s ideal for couples, small families, or business travelers. With its own private entrance, high-speed Wi-Fi, a fully equipped kitchen, and convenient access to downtown Barrie and the GO Station, this apartment has everything you need for a comfortable stay.

Private Basement Suite in a family neighborhood
Its a clean & spacious private Basement suite in a family neighborhood with all amenities that you may require for your stay. Features a queen bed, bathroom and kitchen. Free Parking is included. Highway 400, Park Place, Walmart, Costco, Canadian Tire are within 5-7 minutes driving distance. We offer our guests complete privacy from check-in to check-out, but always available if needed. Perfect for savvy budget travelers who deserve quality stay.

1 Bedroom Hotel Style Short/Long term Available
Come stay at this brand new all-season, private & modern guest suite close to all Innisfil has to offer! 1.2 km away from Lake Simcoe, Big Cedar Golf Course & minutes away from all major Ski hills in Barrie! Enjoy summer activities such as multiple beaches, boating/marinas, golfing & fishing- all within walking range. Enjoy winter activities such as skiing, snowboarding and very special ice fishing spot at the end of the road.

Boardwalk Bliss For Two *1 hr From TO!*
Waterfront Escape – 1 Hour from Toronto! Enjoy a private, street-level retreat steps from the marina boardwalk! Perfect for a relaxing getaway or remote work, with fast WiFi and in-room entertainment. 🌊 Activities Nearby: Waterside Dining & Boardwalk Music Nature Trails, Golf & Spa 🚤 Optional Add-Ons: ✔ Boating Excursions (Pre-Book) ✔ Dining & Activity Combos 📆 Book Now – Dates Fill Fast!

Boho by the Bay
BlogTO writes: " Friday Harbour Resort is a vibrant, upscale destination...That's perfect for a quick getaway..., with plenty of cool restaurants and shops, a waterfront pedestrian village, and year-round recreational activities." I encourage you to search eventsatfridayharbour to see what is seasonally available. if after searching, you still have questions or need clarification, please ask!

Cozy getaway for two with hot tub!
Unwind in our peaceful guest suite attached to our home located near Mount St-Louis Moonstone, Vetta Nordic Spa and the cozy town of Coldwater. With its private entrance, hot tub (accessible daily between 8am and 10pm) and serene forest surroundings, this space is designed for guests who value calm, quiet and nature. We ask that guests share our appreciation for a tranquil environment.
Popular amenities for Orillia family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy Stays – Your Fall Getaway at Friday Harbour

Private 40 Acre Cottage with Hot Tub

Tranquil Retreat private Hot Tub Horseshoe Valley

Riverfront Cottage with HotTub

Oasis Spa w/ Private Sauna!

Mill Pond Cabin, Nordic Cabin w/ Sauna + Hot-tub

Serene Comfort. Hot Tub, Full Suite with Kitchen

Private 2BR Condo | 4 Beds+Pool+Resort
Family- and pet-friendly home rentals

Farmhouse GUEST SUITE; Year round hot tub

Tiny House in Penetanguishene

Woodland Muskoka Tiny House

Glass Dome - Sleep Under The Stars- Free Sundays

Ultimate Georgian Bay Vacation Getaway

Loft on King- Downtown Midland

Modern 2BR Apt | Near Lake + Playground + Fire Pit

Riches Retreat*See description for Special Offers!
Family-friendly home rentals with a pool

Cute and Cozy House

GATED RESORT COTTAGE

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Utopia villa and spa

Mackenzie Cottage

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Beautiful Basement apartment with swimming pool
When is the best time to visit Orillia?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $222 SGD | $179 SGD | $183 SGD | $224 SGD | $213 SGD | $238 SGD | $269 SGD | $265 SGD | $204 SGD | $215 SGD | $194 SGD | $222 SGD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 12°C | 17°C | 20°C | 19°C | 15°C | 9°C | 3°C | -3°C |
Quick stats about holiday rentals that are family-friendly in Orillia

Total holiday rentals
Explore 90 holiday rentals in Orillia

Nightly prices starting at
Orillia holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 2,810 verified reviews to help you choose

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
90 of Orillia holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Orillia rentals

4.8 Average rating
Orillia stays are highly rated by guests – averaging 4.8 out of 5!
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- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Lakeridge Ski Resort
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Rocky Crest Golf Club
- Angus Glen Golf Club
- Gull Lake
- Port Carling Golf & Country Club
- Windermere Golf & Country Club
- The Georgian Peaks Club
- Muskoka Lakes Golf and Country Club
- The Club At Bond Head
- Muskoka Bay Resort
- Dagmar Ski Resort
- Wooden Sticks Golf Club
- Lake Joseph Golf Club
- Bigwin Island Golf Club
- The Georgian Bay Club
- Georgian Bay Islands National Park
- Barrie Country Club
- Alpine Ski Club




